[1-(3-Chloro-phen-yl)-1H-1,2,3-triazol-4-yl]methanol hemihydrate.

The asymmetric unit of the title hydrate, C(9)H(8)ClN(3)O·0.5H(2)O, comprises two independent 1,2,3-triazole mol-ecules and a water mol-ecule of crystallization. The dihedral angles between the six- and five-membered rings in the 1,2,3-triazole mol-ecules are 12.71 (19) and 17.3 (2)°. The most significant different between them is found in the relative orientations of the terminal CH(2)OH groups with one being close to perpendicular to the five-membered ring [N-C-C-O torsion angle = 82.2 (5)°], while in the other mol-ecule, a notable deviation from a perpendicular disposition is found [torsion angle = -60.3 (5)°]. Supra-molecular chains feature in the crystal packing sustained by O-H⋯(O,N) inter-actions along the a-axis direction. The chains are connected via C-H⋯N inter-actions and the resultant layers stack along the b axis.

Related literature

For background to the synthesis, biological activity and structures of 1,2,3-triazole derivatives, see: Boechat et al. (2010 ▶, 2011 ▶); Costa et al. (2006a ▶,b ▶); Ferreira et al. (2007 ▶); Jordão et al. (2009 ▶). For the synthesis, see: Boechat et al. (2011 ▶). For additional geometric analysis, see: Spek (2009 ▶).

Experimental

Crystal data

C9H8ClN3O·0.5H2O

M = 218.64

Triclinic,

a = 6.0078 (4) Å

b = 7.4897 (4) Å

c = 22.3145 (15) Å

α = 88.818 (4)°

β = 89.901 (2)°

γ = 80.493 (4)°

V = 990.07 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 120 K

0.18 × 0.18 × 0.02 mm

Data collection

Bruker–Nonius APEX II CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.843, T max = 1.000

10830 measured reflections

3909 independent reflections

2948 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.163

S = 1.00

3909 reflections

274 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.34 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), QMol (Gans & Shalloway, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811041560/hb6439sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041560/hb6439Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041560/hb6439Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H8ClN3O·0.5H2O	Z = 4
Mr = 218.64	F(000) = 452
Triclinic, P1	Dx = 1.467 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0078 (4) Å	Cell parameters from 19812 reflections
b = 7.4897 (4) Å	θ = 2.9–27.5°
c = 22.3145 (15) Å	µ = 0.36 mm−1
α = 88.818 (4)°	T = 120 K
β = 89.901 (2)°	Plate, colourless
γ = 80.493 (4)°	0.18 × 0.18 × 0.02 mm
V = 990.07 (11) Å3

Bruker–Nonius APEX II CCD camera on κ-goniostat diffractometer	3909 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	2948 reflections with I > 2σ(I)
10cm confocal mirrors	Rint = 0.038
Detector resolution: 9.091 pixels mm-1	θmax = 26.5°, θmin = 2.9°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −9→9
Tmin = 0.843, Tmax = 1.000	l = −28→28
10830 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0446P)2 + 2.5602P] where P = (Fo2 + 2Fc2)/3
3909 reflections	(Δ/σ)max = 0.012
274 parameters	Δρmax = 0.41 e Å−3
5 restraints	Δρmin = −0.34 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.85344 (17)	0.75800 (15)	0.46687 (4)	0.0449 (3)
O1	0.5639 (6)	0.7737 (5)	0.05307 (13)	0.0595 (9)
H1O	0.629 (9)	0.747 (7)	0.0204 (13)	0.089*
N1	0.6411 (5)	0.8503 (4)	0.24523 (13)	0.0297 (6)
N2	0.8433 (5)	0.7528 (4)	0.23011 (14)	0.0386 (7)
N3	0.8614 (6)	0.7674 (4)	0.17193 (14)	0.0424 (8)
C1	0.6580 (6)	0.8250 (5)	0.41004 (15)	0.0304 (7)
C2	0.4384 (6)	0.8954 (5)	0.42488 (16)	0.0343 (8)
H2	0.3932	0.9055	0.4657	0.041*
C3	0.2852 (6)	0.9509 (5)	0.37926 (15)	0.0331 (8)
H3	0.1338	1.0005	0.3889	0.040*
C4	0.3494 (6)	0.9352 (5)	0.31987 (16)	0.0317 (8)
H4	0.2426	0.9724	0.2889	0.038*
C5	0.5708 (6)	0.8647 (4)	0.30588 (15)	0.0280 (7)
C6	0.7280 (6)	0.8092 (5)	0.35095 (15)	0.0314 (8)
H6	0.8801	0.7614	0.3414	0.038*
C7	0.5315 (6)	0.9254 (5)	0.19577 (15)	0.0322 (8)
H7	0.3870	0.9992	0.1940	0.039*
C8	0.6716 (7)	0.8731 (5)	0.14894 (16)	0.0381 (9)
C9	0.6412 (8)	0.9160 (6)	0.08392 (17)	0.0484 (11)
H9A	0.5309	1.0289	0.0784	0.058*
H9B	0.7867	0.9368	0.0665	0.058*
Cl2	0.7137 (2)	0.31120 (15)	0.43211 (4)	0.0519 (3)
O2	1.1922 (7)	0.3320 (5)	0.04279 (18)	0.0843 (14)
H2O	1.219 (12)	0.422 (6)	0.062 (3)	0.126*
N4	0.7744 (5)	0.2978 (4)	0.20400 (13)	0.0306 (6)
N5	0.9702 (5)	0.1798 (5)	0.21008 (15)	0.0433 (8)
N6	1.0590 (6)	0.1604 (5)	0.15647 (16)	0.0485 (9)
C10	0.5956 (6)	0.3531 (5)	0.36144 (16)	0.0348 (8)
C11	0.3706 (6)	0.4305 (5)	0.35577 (16)	0.0359 (8)
H11	0.2793	0.4587	0.3902	0.043*
C12	0.2826 (6)	0.4657 (5)	0.29895 (17)	0.0389 (9)
H12	0.1293	0.5210	0.2943	0.047*
C13	0.4137 (6)	0.4217 (5)	0.24830 (16)	0.0318 (8)
H13	0.3506	0.4445	0.2093	0.038*
C14	0.6367 (6)	0.3444 (4)	0.25557 (16)	0.0309 (8)
C15	0.7315 (6)	0.3090 (5)	0.31195 (16)	0.0323 (8)
H15	0.8855	0.2558	0.3166	0.039*
C16	0.7421 (6)	0.3525 (5)	0.14617 (16)	0.0350 (8)
H16	0.6188	0.4348	0.1298	0.042*
C17	0.9245 (7)	0.2643 (5)	0.11626 (18)	0.0395 (9)
C18	0.9826 (8)	0.2697 (6)	0.05057 (19)	0.0538 (12)
H18A	0.9928	0.1471	0.0339	0.065*
H18B	0.8623	0.3516	0.0287	0.065*
O1W	1.2489 (5)	0.6147 (4)	0.10634 (13)	0.0491 (7)
H1W	1.143 (6)	0.661 (6)	0.1286 (19)	0.074*
H2W	1.293 (8)	0.698 (5)	0.086 (2)	0.074*

	U11	U22	U33	U12	U13	U23
Cl1	0.0387 (5)	0.0620 (7)	0.0332 (5)	−0.0063 (4)	−0.0052 (4)	0.0013 (4)
O1	0.081 (2)	0.077 (2)	0.0334 (15)	−0.0501 (19)	0.0214 (15)	−0.0252 (15)
N1	0.0308 (16)	0.0279 (15)	0.0314 (15)	−0.0076 (12)	0.0057 (12)	−0.0036 (12)
N2	0.0380 (18)	0.0384 (18)	0.0380 (17)	−0.0016 (14)	0.0155 (14)	−0.0037 (13)
N3	0.049 (2)	0.0433 (19)	0.0375 (18)	−0.0135 (15)	0.0174 (16)	−0.0073 (14)
C1	0.0303 (18)	0.0333 (19)	0.0288 (17)	−0.0085 (14)	−0.0026 (14)	−0.0010 (14)
C2	0.037 (2)	0.039 (2)	0.0283 (18)	−0.0112 (16)	0.0055 (16)	−0.0051 (15)
C3	0.0289 (18)	0.039 (2)	0.0310 (18)	−0.0040 (15)	0.0073 (15)	−0.0030 (15)
C4	0.0339 (19)	0.0316 (19)	0.0298 (18)	−0.0061 (14)	0.0050 (15)	−0.0024 (14)
C5	0.0308 (18)	0.0259 (17)	0.0283 (17)	−0.0074 (13)	0.0036 (14)	−0.0025 (13)
C6	0.0280 (18)	0.0317 (19)	0.0348 (19)	−0.0056 (14)	0.0070 (15)	−0.0043 (14)
C7	0.0345 (19)	0.0354 (19)	0.0290 (18)	−0.0120 (15)	0.0024 (15)	−0.0039 (14)
C8	0.048 (2)	0.038 (2)	0.0327 (19)	−0.0193 (17)	0.0104 (17)	−0.0109 (16)
C9	0.070 (3)	0.051 (3)	0.032 (2)	−0.032 (2)	0.014 (2)	−0.0089 (18)
Cl2	0.0633 (7)	0.0630 (7)	0.0319 (5)	−0.0187 (5)	−0.0054 (5)	0.0050 (4)
O2	0.093 (3)	0.094 (3)	0.085 (3)	−0.067 (2)	0.063 (2)	−0.049 (2)
N4	0.0293 (15)	0.0294 (15)	0.0333 (16)	−0.0048 (12)	0.0040 (12)	−0.0042 (12)
N5	0.0298 (17)	0.050 (2)	0.047 (2)	0.0020 (14)	0.0020 (15)	−0.0105 (15)
N6	0.0359 (19)	0.057 (2)	0.053 (2)	−0.0086 (16)	0.0100 (17)	−0.0177 (17)
C10	0.043 (2)	0.034 (2)	0.0289 (18)	−0.0136 (16)	−0.0044 (16)	0.0042 (14)
C11	0.041 (2)	0.036 (2)	0.0318 (19)	−0.0101 (16)	0.0087 (16)	−0.0011 (15)
C12	0.034 (2)	0.036 (2)	0.045 (2)	−0.0018 (16)	0.0087 (17)	−0.0016 (16)
C13	0.0333 (19)	0.0312 (19)	0.0316 (18)	−0.0075 (14)	−0.0006 (15)	−0.0011 (14)
C14	0.0329 (19)	0.0259 (18)	0.0355 (19)	−0.0087 (14)	0.0080 (15)	−0.0039 (14)
C15	0.0308 (19)	0.0333 (19)	0.0340 (19)	−0.0086 (14)	−0.0009 (15)	0.0027 (14)
C16	0.041 (2)	0.034 (2)	0.0316 (19)	−0.0113 (16)	0.0063 (16)	−0.0002 (15)
C17	0.044 (2)	0.038 (2)	0.042 (2)	−0.0190 (17)	0.0149 (18)	−0.0105 (17)
C18	0.061 (3)	0.063 (3)	0.046 (2)	−0.033 (2)	0.026 (2)	−0.019 (2)
O1W	0.0453 (17)	0.065 (2)	0.0381 (16)	−0.0109 (14)	0.0155 (13)	−0.0064 (14)

Cl1—C1	1.739 (4)	O2—C18	1.423 (5)
O1—C9	1.422 (5)	O2—H2O	0.840 (10)
O1—H1O	0.839 (10)	N4—C16	1.350 (4)
N1—C7	1.350 (4)	N4—N5	1.355 (4)
N1—N2	1.356 (4)	N4—C14	1.431 (4)
N1—C5	1.418 (4)	N5—N6	1.310 (5)
N2—N3	1.307 (4)	N6—C17	1.353 (5)
N3—C8	1.370 (5)	C10—C11	1.385 (5)
C1—C2	1.380 (5)	C10—C15	1.385 (5)
C1—C6	1.385 (5)	C11—C12	1.378 (5)
C2—C3	1.384 (5)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.390 (5)
C3—C4	1.382 (5)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.377 (5)
C4—C5	1.385 (5)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.384 (5)
C5—C6	1.390 (5)	C15—H15	0.9500
C6—H6	0.9500	C16—C17	1.364 (5)
C7—C8	1.363 (5)	C16—H16	0.9500
C7—H7	0.9500	C17—C18	1.507 (5)
C8—C9	1.485 (5)	C18—H18A	0.9900
C9—H9A	0.9900	C18—H18B	0.9900
C9—H9B	0.9900	O1W—H1W	0.840 (10)
Cl2—C10	1.731 (4)	O1W—H2W	0.838 (10)
C9—O1—H1O	115 (4)	C16—N4—N5	110.3 (3)
C7—N1—N2	110.3 (3)	C16—N4—C14	130.2 (3)
C7—N1—C5	128.6 (3)	N5—N4—C14	119.5 (3)
N2—N1—C5	121.1 (3)	N6—N5—N4	106.6 (3)
N3—N2—N1	106.9 (3)	N5—N6—C17	109.9 (3)
N2—N3—C8	109.7 (3)	C11—C10—C15	121.9 (3)
C2—C1—C6	121.7 (3)	C11—C10—Cl2	119.7 (3)
C2—C1—Cl1	119.3 (3)	C15—C10—Cl2	118.5 (3)
C6—C1—Cl1	119.0 (3)	C12—C11—C10	118.3 (3)
C1—C2—C3	118.8 (3)	C12—C11—H11	120.8
C1—C2—H2	120.6	C10—C11—H11	120.8
C3—C2—H2	120.6	C11—C12—C13	121.3 (4)
C4—C3—C2	120.9 (3)	C11—C12—H12	119.4
C4—C3—H3	119.6	C13—C12—H12	119.4
C2—C3—H3	119.6	C14—C13—C12	118.9 (3)
C3—C4—C5	119.5 (3)	C14—C13—H13	120.6
C3—C4—H4	120.3	C12—C13—H13	120.6
C5—C4—H4	120.3	C13—C14—C15	121.4 (3)
C6—C5—C4	120.7 (3)	C13—C14—N4	119.7 (3)
C6—C5—N1	119.0 (3)	C15—C14—N4	118.8 (3)
C4—C5—N1	120.4 (3)	C14—C15—C10	118.2 (3)
C5—C6—C1	118.5 (3)	C14—C15—H15	120.9
C5—C6—H6	120.7	C10—C15—H15	120.9
C1—C6—H6	120.7	N4—C16—C17	105.2 (3)
N1—C7—C8	105.6 (3)	N4—C16—H16	127.4
N1—C7—H7	127.2	C17—C16—H16	127.4
C8—C7—H7	127.2	N6—C17—C16	108.0 (3)
C7—C8—N3	107.5 (3)	N6—C17—C18	122.0 (4)
C7—C8—C9	129.8 (4)	C16—C17—C18	129.9 (4)
N3—C8—C9	122.7 (3)	O2—C18—C17	109.9 (4)
O1—C9—C8	111.6 (3)	O2—C18—H18A	109.7
O1—C9—H9A	109.3	C17—C18—H18A	109.7
C8—C9—H9A	109.3	O2—C18—H18B	109.7
O1—C9—H9B	109.3	C17—C18—H18B	109.7
C8—C9—H9B	109.3	H18A—C18—H18B	108.2
H9A—C9—H9B	108.0	H1W—O1W—H2W	109 (4)
C18—O2—H2O	120 (5)
C7—N1—N2—N3	0.5 (4)	C16—N4—N5—N6	−0.2 (4)
C5—N1—N2—N3	−179.0 (3)	C14—N4—N5—N6	179.2 (3)
N1—N2—N3—C8	−0.3 (4)	N4—N5—N6—C17	0.3 (4)
C6—C1—C2—C3	0.1 (5)	C15—C10—C11—C12	−0.7 (5)
Cl1—C1—C2—C3	179.0 (3)	Cl2—C10—C11—C12	178.7 (3)
C1—C2—C3—C4	0.5 (5)	C10—C11—C12—C13	1.3 (5)
C2—C3—C4—C5	−0.7 (5)	C11—C12—C13—C14	−1.1 (5)
C3—C4—C5—C6	0.3 (5)	C12—C13—C14—C15	0.4 (5)
C3—C4—C5—N1	−178.9 (3)	C12—C13—C14—N4	179.9 (3)
C7—N1—C5—C6	−166.4 (3)	C16—N4—C14—C13	17.2 (5)
N2—N1—C5—C6	12.9 (5)	N5—N4—C14—C13	−162.1 (3)
C7—N1—C5—C4	12.8 (5)	C16—N4—C14—C15	−163.2 (3)
N2—N1—C5—C4	−167.9 (3)	N5—N4—C14—C15	17.4 (5)
C4—C5—C6—C1	0.3 (5)	C13—C14—C15—C10	0.1 (5)
N1—C5—C6—C1	179.5 (3)	N4—C14—C15—C10	−179.4 (3)
C2—C1—C6—C5	−0.5 (5)	C11—C10—C15—C14	0.0 (5)
Cl1—C1—C6—C5	−179.4 (3)	Cl2—C10—C15—C14	−179.4 (3)
N2—N1—C7—C8	−0.4 (4)	N5—N4—C16—C17	0.1 (4)
C5—N1—C7—C8	179.0 (3)	C14—N4—C16—C17	−179.3 (3)
N1—C7—C8—N3	0.2 (4)	N5—N6—C17—C16	−0.3 (4)
N1—C7—C8—C9	−179.4 (3)	N5—N6—C17—C18	−179.8 (3)
N2—N3—C8—C7	0.1 (4)	N4—C16—C17—N6	0.1 (4)
N2—N3—C8—C9	179.7 (3)	N4—C16—C17—C18	179.6 (4)
C7—C8—C9—O1	−98.3 (5)	N6—C17—C18—O2	−60.3 (5)
N3—C8—C9—O1	82.2 (5)	C16—C17—C18—O2	120.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O2i	0.84 (4)	1.82 (4)	2.651 (5)	170 (5)
O2—H2o···O1w	0.84 (6)	1.80 (5)	2.641 (5)	174 (7)
O1w—H1w···N3	0.84 (4)	2.00 (4)	2.837 (5)	172 (4)
O1w—H2w···O1ii	0.84 (4)	1.95 (5)	2.663 (5)	142 (4)
C16—H16···O1wiii	0.95	2.45	3.383 (5)	166
C7—H7···N6iv	0.95	2.28	3.197 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O2i	0.84 (4)	1.82 (4)	2.651 (5)	170 (5)
O2—H2o⋯O1w	0.84 (6)	1.80 (5)	2.641 (5)	174 (7)
O1w—H1w⋯N3	0.84 (4)	2.00 (4)	2.837 (5)	172 (4)
O1w—H2w⋯O1ii	0.84 (4)	1.95 (5)	2.663 (5)	142 (4)
C16—H16⋯O1wiii	0.95	2.45	3.383 (5)	166
C7—H7⋯N6iv	0.95	2.28	3.197 (5)	161

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .